Mentoring In A Virtual World

Before I jump into the topic, I would like to address whether you need a mentor or not. The answer is yes. It will always be yes.

Elaborate? OK, just a bit. This is coming from the experience I have as an entrepreneur and someone who gets to mentor and witness scores of entrepreneurs being mentored each year. No matter how successful you have been and despite all that you know—you cannot know it all. It is also nearly impossible to keep a separated, impartial perspective when you are buried in startup building. Having someone that can offer insights that you may have missed, allow you to vent, question, doubt, test, etc., without recourse is invaluable. A mentor is a safe set of ears and mind that can help you think through things and hopefully help you avoid issues that can be costly. So yes, a mentor is a good thing to have because many entrepreneurs live in an echo chamber of encouragement rather than real talk that is meant to challenge and improve.

The “virtual world” has done two things that are positive when it comes to mentoring—removing place and greatly flexing time. It has also done two more negative things—strained personal connections and increased the need for entrepreneur discipline.

Finding a mentor takes effort. There are multiple ways to make it happen and here are a few common ones that work in our virtual world, as well as when things are what used to pass for as normal:


Economic or venture development organizations

Many of these groups have mentoring available for free that is provided by experienced mentors looking to give back on a personal level. JumpStart has multiple established mentoring programs to assist entrepreneurs.


Social Media

I am not advocating using Twitter, Medium, Reddit, etc., as an endless scrolling exercise. Start following people that have the background you need. Read and understand their thoughts, knowledge, opinions and how they interact with people online. Then reach out. What do you have to lose? Ask something relevant, succinct and that will interest them. Continue from there establishing a relationship. Not in a creepy way, but in a professional manner that would allow you at some point to ask for a more formal mentoring relationship.

LinkedIn searches are limited but you would be amazed at who you can find without registering for premium. Look for people that have the experience that would help you and reach out. There are techniques for doing this that are far beyond what this blog can cover but remember—flattery will get you everywhere. Plus, people like to help other people that know they need help.


People That You Know

You know people. Ask them if they know anyone. Ask the people they know if they know anyone. Repeat. That is how a network operates. It is not just who you know, it is who those people know. If you know three people and they each know three people, you already have access to nine more people. Do the math – you can reach a ton of people just by asking a small group of your own contacts.


Virtual conferences

They work like a real-world conference but without having to pay to travel. Attend them and find people that are where you want to be.


Now, let’s assume you have found a mentor or two and they agree to start to work with you. You are going to have to earn their continued help and it is best to consider yourself in the dating mode. The relationship is mutual, and you must make it worth them becoming professionally and personally invested in seeing you succeed. That does not mean paying them. It means they need the opportunity to learn and to see you utilize their time wisely to increase your chances of success. They want to see their advice put to good use.

The keys to maintaining the mentor relationship revolve around your effort. Some things to do that will enhance the experience and keep your mentor engaged are:

  • Setting appointments for meetings and keep them
  • Sending an agenda prior to the meeting
  • Being organized and have a defined intent for what you wish to get out of the session
  • Showing progress – no mentor wants to work with an entrepreneur that is not moving forward
  • Being diligent in your efforts
  • Being honest – there is no reason to hide things from your mentor
  • Being grateful – “thank you” goes a long way
  • Listening to the advice, consider it and use that which makes sense
  • Asking what you can do for them – you have talents, networks, experiences that may be of benefit for the mentor. I have seen where an entrepreneur taught the mentor’s child how to play guitar.

Some of the things that the virtual world has provided should also be used to your advantage:

  • You do not have to drive to meetings. They can be shorter and to the point since the time invested in getting there does not exist.
  • Use video for most of the meetings. The emotion is important as are what both parties are conveying.
  • You can have short “in-between” interactions that do not entail a full meeting but hit an issue that you face.
  • Report on important achievements. Mentors are like parents. When they hear you have a big meeting coming up with a potential investor or customer, they want to hear how it went. Pick up the phone and call.
  • Email is OK but a phone call or video call is much better. Your mentor cannot interact with an email. It is more acceptable to reach out to people due to the relative isolation that everyone has experienced.
  • Mix in physical meetings if possible. Many people will not have a problem with grabbing a coffee from a shop and sitting outside.


The advice above boils down to some of the core qualities that come with being an entrepreneur. Make the effort, be creative, be diligent and listen. No one asked for our virtual world, but it has permanently changed how we operate. Mentoring is no different. It is still just as important, but it takes a new approach to find the mentors that will really help your business take off.